153364-63-7

Usage

Uses

Used in Pharmaceutical Industry:
m-PEG4-benzaldehyde is used as a molecular linker for improving the solubility of drugs in aqueous solutions, which is crucial for the development of effective pharmaceutical formulations.
Used in Cancer Therapy:
m-PEG4-benzaldehyde is used as a component in the development of biotin-decorated NIR (near-infrared) absorbing nanosheets for targeted photodynamic cancer therapy. This application leverages the molecule's ability to enhance solubility and facilitate the targeted delivery of therapeutic agents to cancer cells, improving the efficacy of treatment and reducing side effects on healthy tissues.

Upstream product

• 62921-74-8 2-(2-(2-methoxyethoxy)ethoxy)ethyl p-toluenesulfonate 
• 123-08-0 4-hydroxy-benzaldehyde 
• 74654-05-0 8-methoxy-1-(methylsulfonyl)oxy-3,6-dioxaoctane 
• 72593-77-2 3,6,9-trioxadecyl bromide 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 112-35-6 triethylene glucol monomethyl ether 

Downstream Products

• 153364-64-8 α-cyano-N-(2-phenethyl)-p-(1,4,7,10-tetraoxaundecyl)benzylamine 
• 1266698-88-7 C₄₇H₅₅BF₂N₂O₉ 
• 1266698-90-1 C₅₇H₆₅BF₂N₂O₁₁ 
• 1380861-87-9 C₃₃H₃₇BF₂N₂O₅ 
• 22112-83-0 5,10,15,20-tetrakis(4-methoxycarbonylphenyl)porphyrin 
• 1579250-71-7 C₄₆H₅₉BF₂N₂O₁₀ 
• 1579250-73-9 C₄₃H₅₃BF₂N₂O₁₀ 

Relevant academic research and scientific papers

Synthesis and characterization of trans-di-(4-pyridyl)porphyrin dimers

Preparation and characterization of a small library of symmetric trans-di(4-pyridyl)porphyrin dimers, obtained by either Glaser-Hay or Sonogashira coupling reactions from appropriately prepared trans-di-4-pyridylporphyrin precursors, is presented. The porphyrin dimers are differentiated by a phenyl-alkynyl bridge of increasing length at one meso-position, while for all the derivatives the two remaining opposite meso-positions are tailored with a phenyl moiety bearing a short polyether chain. Coordination of the four pyridyl groups with appropriate metal fragments may be exploited to construct tubular hollow structures, with varied internal sizes, depending on the choice of the porphyrin dimer component.

Reductive alkylation of proteins using iridium catalyzed transfer hydrogenation

An efficient transition metal catalyzed procedure for the reductive alkylation of proteins has been developed. Imines formed from the condensation of aldehydes (1 mM) with lysine residues and the N-terminus can be reduced efficiently by a [Cp*Ir(4,4′-dime

Development and characterization of nanoparticles prepared from the mixture of triterpenoids and amphiphilic meso-arylporphirins

The mixture of triterpenoids from birch bark and amphiphilic meso-arylprophyrins was used to develop spherical amorphous nanoparticles. The nanoparticles were studied with the methods of electron microscopy, dynamic light scattering, UV spectroscopy, and

Photogeneration of Singlet Oxygen by Tetra(p-Hydroxyphenyl)porphyrins Modified with Oligo- and Polyalkylene Oxides

Abstract: Mono- and diethylene oxide derivatives of tetra(p-hydroxyphenyl)porphyrin (THPP) with different conformation states are synthesized. These compounds exhibit high photosensitization activity in the generation of singlet oxygen in organic and aque

Synthesis of asymmetric tetraarylporphyrins and their ytterbium complexes

The synthesis of asymmetric meso-aryl-substituted porphyrins containing three 4-methoxycarbonylphenyl groups, and 4-hydroxyphenyl or 4-hydroxy-3-methoxyphenyl radicals or isomeric 3-and 4-pyridyl radicals as a forth substitute, is described. 4-Oxyalkyl derivatives are obtained. The ytterbium complexes of these porphyrins have been synthesized, and their spectral luminescence properties have been studied. A significant difference in the lifetimes of the excited state of ytterbium complexes of the esters and acids of asymmetric porphyrins has been shown. Pleiades Publishing, Ltd., 2011.

Biotin-decorated NIR-absorbing nanosheets for targeted photodynamic cancer therapy

Targeted photodynamic therapy (PDT) is one of the promising approaches for the selective killing of cancerous cells without affecting the normal cells, and hence designing new strategies for targeted PDT is extremely important. Herein we report the design and synthesis of a new class of nanosheets derived from the self-assembly of the iodo-BODIPY-biotin conjugate as a photosensitizer for targeted PDT applications. The nanosheet exhibits a high extinction coefficient in the NIR region, high singlet oxygen efficiency, no toxicity in the dark and cell targeting ligands (biotin) on the surface, which are necessary features required for an ideal photosensitizer. Overexpression of sodium-dependent multivitamin transporters (SMVTs) in HeLa and A549 (biotin receptor positive cell lines) is explored for the selective uptake of the nanophotosensitizer through receptor mediated endocytosis (interaction between biotin and SMVT). Control experiments using a biotin receptor negative cell line (WI-38) are also carried out to confirm that the specific interaction between the SMVTs and biotin is mainly responsible for the selective uptake of the photosensitizer. Efficient killing of cancerous cells is demonstrated upon light irradiation through the generation of singlet oxygen and other reactive oxygen species around the cellular environment.

An Ethacrynic Acid-Brominated BODIPY Photosensitizer (EA-BPS) Construct Enhances the Lethality of Reactive Oxygen Species in Hypoxic Tumor-Targeted Photodynamic Therapy

Despite being a clinically approved intervention for cancer, photodynamic therapy (PDT) still suffers from limitations. Prime among these is a therapeutic response that is mostly oxygen dependent. This limits the utility of PDT in treating hypoxic tumors

Fluorescent multi-component polymer sensors for the sensitive and selective detection of Hg2+/Hg+ions: Via dual mode fluorescence and colorimetry

Multi-component polymers (MCPs) incorporate multiple components into the main chain or pendant group and have special functions. In this work, the small-molecule fluorescent boron-dipyrromethene (BODIPY), with ester groups and/or alkoxyl long chains, was synthesized first. Then, this small-molecule BODIPY and the components containing CC bonds (HD and PD) were reacted via the Heck coupling reaction to obtain macromolecular probes that perform different functions. With the help of ester groups and alkoxyl "tail", polymers MCP1 and MCP2 were soluble in a variety of water-miscible organic solvents. Moreover, MCP3 and MCP4 were completely soluble in water. These macromolecular probes showed sensitive and selective recognition toward Hg2+/Hg+ because of the introduced components (HD and PD) containing CC bonds. After binding to Hg2+/Hg+, MCP1 and MCP2 demonstrated fluorescence quenching and color changes, which allowed the dual-channel specific detection of Hg2+/Hg+. Compared with the probes containing HD, the probes containing PD showed higher sensitivity, and the good recognition ability caused the detection limit to be as low as 0.32 μM, which may be due to the "molecular wire"mechanism. The small-molecule components with different functional groups were polymerized into fluorescent polymer materials. This methodology endows the polymer probe with good solubility and high sensitivity, and the as-prepared polymers could sense metal ions in aqueous environments. This journal is

A tumor-targeted Photodynamic therapeutic compound

The present invention relates to a tumor targeting photodynamic therapeutic agent containing a compound represented by chemical formula 1. The compound according to the present invention can significantly improve cancer treatment efficiency.COPYRIGHT KIPO 2019

Family of BODIPY Photocages Cleaved by Single Photons of Visible/Near-Infrared Light

Photocages are light-sensitive chemical protecting groups that provide external control over when, where, and how much of a biological substrate is activated in cells using targeted light irradiation. Regrettably, most popular photocages (e.g., o-nitrobenzyl groups) absorb cell-damaging ultraviolet wavelengths. A challenge with achieving longer wavelength bond-breaking photochemistry is that long-wavelength-absorbing chromophores have shorter excited-state lifetimes and diminished excited-state energies. However, here we report the synthesis of a family of BODIPY-derived photocages with tunable absorptions across the visible/near-infrared that release chemical cargo under irradiation. Derivatives with appended styryl groups feature absorptions above 700 nm, yielding photocages cleaved with the highest known wavelengths of light via a direct single-photon-release mechanism. Photorelease with red light is demonstrated in living HeLa cells, Drosophila S2 cells, and bovine GM07373 cells upon ～5 min irradiation. No cytotoxicity is observed at 20 μM photocage concentration using the trypan blue exclusion assay. Improved B-alkylated derivatives feature improved quantum efficiencies of photorelease ～20-fold larger, on par with the popular o-nitrobenzyl photocages (?φ = 50-100 M-1 cm-1), but absorbing red/near-IR light in the biological window instead of UV light.